Identification

Name
Cefdinir
Accession Number
DB00535  (APRD00644)
Type
Small Molecule
Groups
Approved
Description

Cefdinir (marketed by Abbott Laboratories under the brand name Omnicef) is a semi-synthetic, broad-spectrum antibiotic in the third generation of the cephalosporin class, proven effective for common bacterial infections of the ear, sinus, throat, and skin. It was approved by the U.S. Food and Drug Administration (FDA) in December of 1997.

Structure
Thumb
Synonyms
  • (6R,7R,Z)-7-(2-(2-Aminothiazol-4-yl)-2-(hydroxyimino)acetamido)-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-hydroxyimino]-acetylamino}-8-oxo-3-vinyl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Cefdinir
  • Cefdinirum
  • CFDN
External IDs
BMY-28488 / CI 983 / CI-983 / FK 482 / FK-482
Product Ingredients
IngredientUNIICASInChI Key
Cefdinir monohydrate6E7SN358SE213978-34-8QWUVJQSNISEEQI-KYIYMPJCSA-N
Product Images
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
CefdinirPowder, for suspension250 mg/5mLOralProficient Rx LP2007-05-08Not applicableUs
CefdinirPowder, for suspension250 mg/5mLOralAidarex Pharmaceuticals LLC2007-05-01Not applicableUs
CefdinirCapsule300 mg/1OralProficient Rx LP2014-07-04Not applicableUs
CefdinirPowder, for suspension125 mg/5mLOralNu Care Pharmaceauticals,inc.2013-10-04Not applicableUs
CefdinirCapsule300 mg/1OralLake Erie Medical Dba Quality Care Produts Llc2014-05-01Not applicableUs
CefdinirCapsule300 mg/1OralSandoz2007-04-06Not applicableUs00781 2176 60 nlmimage10 6939b4bd
CefdinirPowder, for suspension125 mg/5mLOralNucare Pharmaceuticals, Inc.2007-05-08Not applicableUs
CefdinirCapsule300 mg/1OralPhysicians Total Care, Inc.2007-05-08Not applicableUs
CefdinirPowder, for suspension125 mg/5mLOralLupin Pharmaceuticals2007-05-01Not applicableUs
CefdinirCapsule300 mg/1OralPd Rx Pharmaceuticals, Inc.2014-07-04Not applicableUs
International/Other Brands
Cednir (Abbott) / Cefdiel (Ranbaxy) / Cefzon (Astellas) / Duocef (Ranbaxy) / Efdinir (Incepta) / Idinir (Invision) / Kefnir (Glenmark) / Nirocef (Sel-J) / Oceph (Zuventus) / Omicef (Sel-J) / Omnicef (Abbott Laboratories) / Omnicef R (Janssen) / Palacef (Renata) / Palcef (Renata) / Rtist (Lupin) / Samnir (Siam Bheasach) / Xi Fu Ni (Central Pharm) / Zefdinir (Zydus) / Zinir (FDC)
Categories
UNII
CI0FAO63WC
CAS number
91832-40-5
Weight
Average: 395.414
Monoisotopic: 395.035809931
Chemical Formula
C14H13N5O5S2
InChI Key
RTXOFQZKPXMALH-GHXIOONMSA-N
InChI
InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1
IUPAC Name
(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(N-hydroxyimino)acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
SMILES
[H][[email protected]]12SCC(C=C)=C(N1C(=O)[[email protected]]2NC(=O)C(=N/O)\C1=CSC(N)=N1)C(O)=O

Pharmacology

Indication

For the treatment of the respiratory, skin, soft tissue, and ENT infections caused by H. influenzae (including b-lactamase producing strains), H. parainfluenzae (including b-lactamase producing strains), S. pneumoniae (penicillin-susceptible strains), S. pyogenes, S. aureus (including b-lactamase producing strains), and M. catarrhalis.

Structured Indications
Pharmacodynamics

Cefdinir is a third generation cephalosporin with a broad spectrum of activity against enteric gram-negative rods. Cefdinir is stable in the presence of some, but not all, b-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins are susceptible to cefdinir. Cephalosporins work the same way as penicillins: they interfere with the peptidoglycan synthesis of the bacterial wall by inhibiting the final transpeptidation needed for the cross-links. This effect is bactericidal.

Mechanism of action

As with other cephalosporins, bactericidal activity of cefdinir results from inhibition of cell wall synthesis by acting on penicillin binding proteins (PBPs).

TargetActionsOrganism
APenicillin-binding protein 2
inhibitor
Neisseria gonorrhoeae
APBP3
inhibitor
Haemophilus influenzae
NMyeloperoxidase
inhibitor
Human
Absorption

Maximal plasma cefdinir concentrations occur 2 to 4 hours postdose following capsule or suspension administration. Estimated bioavailability of cefdinir capsules is 21% following administration of a 300 mg capsule dose, and 16% following administration of a 600 mg capsule dose. Estimated absolute bioavailability of cefdinir suspension is 25%. Absorption is reduced by approximately 15% when administered with a high fat meal.

Volume of distribution
  • 0.35±0.29 L/kg [adult subjects]
  • 0.67±0.38 L/kg [pediatric subjects (age 6 months to 12 years)]
Protein binding

60%-70%, binding is independent of concentration.

Metabolism

Cefdinir is not appreciably metabolized. Activity is primarily due to parent drug.

Route of elimination

Cefdinir is not appreciably metabolized. Cefdinir is eliminated principally via renal excretion with a mean plasma elimination half-life (t½) of 1.7 (±0.6) hours.

Half life

1.7 ± 0.6 hours

Clearance
  • renal cl=2 +/- 1 mL/min/kg [healthy]
Toxicity

Information on cefdinir overdosage in humans is not available. In acute rodent toxicity studies, a single oral 5600-mg/kg dose produced no adverse effects. Toxic signs and symptoms following overdosage with other b-lactam antibiotics have included nausea, vomiting, epigastric distress, diarrhea, and convulsions.

Affected organisms
  • Enteric gram-negative rods
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Cefdinir.Investigational
Ferric CarboxymaltoseThe serum concentration of Cefdinir can be decreased when it is combined with Ferric Carboxymaltose.Approved
Ferric CitrateThe serum concentration of Cefdinir can be decreased when it is combined with Ferric Citrate.Approved, Investigational
Ferric pyrophosphateThe serum concentration of Cefdinir can be decreased when it is combined with Ferric pyrophosphate.Approved
IronThe serum concentration of Cefdinir can be decreased when it is combined with Iron.Approved
Iron DextranThe serum concentration of Cefdinir can be decreased when it is combined with Iron Dextran.Approved, Vet Approved
Iron saccharateThe serum concentration of Cefdinir can be decreased when it is combined with Iron saccharate.Approved
Picosulfuric acidThe therapeutic efficacy of Picosulfuric acid can be decreased when used in combination with Cefdinir.Approved
Food Interactions
  • Avoid taking antacids at same time (up to 2 hours before or after antibiotic).
  • Avoid taking iron preparations at same time (up to 2 hours before or after antibiotic).
  • Take without regard to meals.

References

Synthesis Reference

Gwan Sun Lee, Young Kil Chang, Jong Pil Chun, Joon Hyung Koh, "Process for preparation of cefdinir." U.S. Patent US6093814, issued December, 1995.

US6093814
General References
  1. Yamanaka H, Shimazaki J, Imai K, Sugiyama Y, Shida K: Effect of estrogen administration on activities of testosterone 5alpha-reductase, alkaline phosphatase and arginase in the ventral and the dorsolateral prostates of rats. Endocrinol Jpn. 1975 Aug;22(4):297-302. [PubMed:1201739]
External Links
Human Metabolome Database
HMDB14675
KEGG Drug
D00917
KEGG Compound
C08110
PubChem Compound
6915944
PubChem Substance
46505573
ChemSpider
5291705
ChEBI
3485
ChEMBL
CHEMBL927
Therapeutic Targets Database
DAP000436
PharmGKB
PA164768739
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Cefdinir
ATC Codes
J01DD15 — Cefdinir
FDA label
Download (69.2 KB)
MSDS
Download (57 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0RecruitingTreatmentOsteomyelitis1
1CompletedNot AvailableHealthy Volunteers2
1CompletedTreatmentHealthy Volunteers4
2, 3CompletedTreatmentAcute Otitis Media1
4CompletedNot AvailableHealthy Volunteers3
4CompletedTreatmentAcute Bacterial Sinusitis (ABS)2
4CompletedTreatmentAcute Otitis Media2
4CompletedTreatmentMild to Moderate Uncomplicated Skin and Skin Structure Infections1
4RecruitingTreatmentAntibiotics / Pituitary Adenomas1
4RecruitingTreatmentPneumonia1
Not AvailableCompletedTreatmentKwashiorkor / Marasmus1
Not AvailableCompletedTreatmentSnoring / Strep Throat1

Pharmacoeconomics

Manufacturers
  • Aurobindo pharma ltd
  • Lupin ltd
  • Orchid healthcare
  • Sandoz inc
  • Teva pharmaceuticals usa
  • Abbott laboratories
Packagers
Dosage forms
FormRouteStrength
CapsuleOral300 mg/1
Powder, for suspensionOral125 mg/5mL
Powder, for suspensionOral250 mg/5mL
Prices
Unit descriptionCostUnit
Omnicef 125 mg/5ml Suspension 100ml Bottle101.59USD bottle
Cefdinir 125 mg/5ml Suspension 60ml Bottle53.05USD bottle
Omnicef 300 mg capsule6.31USD capsule
Omnicef 300 mg omni-pac capsule5.72USD capsule
Cefdinir 300 mg capsule5.22USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4935507No1994-12-042011-12-04Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP-0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0878 mg/mLALOGPS
logP0.02ALOGPS
logP-1.7ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)1.74ChemAxon
pKa (Strongest Basic)7.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area158.21 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.34 m3·mol-1ChemAxon
Polarizability36.12 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.7692
Blood Brain Barrier-0.9659
Caco-2 permeable-0.7205
P-glycoprotein substrateNon-substrate0.5185
P-glycoprotein inhibitor INon-inhibitor0.9298
P-glycoprotein inhibitor IINon-inhibitor0.9165
Renal organic cation transporterNon-inhibitor0.8919
CYP450 2C9 substrateNon-substrate0.8676
CYP450 2D6 substrateNon-substrate0.8203
CYP450 3A4 substrateNon-substrate0.5821
CYP450 1A2 substrateNon-inhibitor0.7603
CYP450 2C9 inhibitorNon-inhibitor0.8303
CYP450 2D6 inhibitorNon-inhibitor0.894
CYP450 2C19 inhibitorNon-inhibitor0.8044
CYP450 3A4 inhibitorNon-inhibitor0.8436
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.953
Ames testNon AMES toxic0.6686
CarcinogenicityNon-carcinogens0.8339
BiodegradationNot ready biodegradable0.9925
Rat acute toxicity1.8801 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9878
hERG inhibition (predictor II)Non-inhibitor0.8964
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-2983000000-72bf1ac3398fbaa1531b

Taxonomy

Description
This compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Cephalosporins
Alternative Parents
N-acyl-alpha amino acids and derivatives / 2,4-disubstituted thiazoles / 1,3-thiazines / 2-amino-1,3-thiazoles / Tertiary carboxylic acid amides / Ketoximes / Heteroaromatic compounds / Secondary carboxylic acid amides / Amino acids / Azetidines
show 10 more
Substituents
Cephalosporin / N-acyl-alpha amino acid or derivatives / Alpha-amino acid or derivatives / 2,4-disubstituted 1,3-thiazole / Meta-thiazine / 1,3-thiazol-2-amine / Azole / Ketoxime / Tertiary carboxylic acid amide / Thiazole
show 24 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
cephalosporin, ketoxime (CHEBI:3485)

Targets

Kind
Protein
Organism
Neisseria gonorrhoeae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Synthesis of cross-linked peptidoglycan from the lipid intermediates.
Gene Name
penA
Uniprot ID
P08149
Uniprot Name
Penicillin-binding protein 2
Molecular Weight
63649.54 Da
References
  1. Ochiai S, Sekiguchi S, Hayashi A, Shimadzu M, Ishiko H, Matsushima-Nishiwaki R, Kozawa O, Yasuda M, Deguchi T: Decreased affinity of mosaic-structure recombinant penicillin-binding protein 2 for oral cephalosporins in Neisseria gonorrhoeae. J Antimicrob Chemother. 2007 Jul;60(1):54-60. Epub 2007 May 31. [PubMed:17540669]
Kind
Protein
Organism
Haemophilus influenzae
Pharmacological action
Yes
Actions
Inhibitor
General Function
Penicillin binding
Specific Function
Not Available
Gene Name
pbp3
Uniprot ID
Q60FT7
Uniprot Name
PBP3
Molecular Weight
67295.025 Da
References
  1. Sanbongi Y, Suzuki T, Osaki Y, Senju N, Ida T, Ubukata K: Molecular evolution of beta-lactam-resistant Haemophilus influenzae: 9-year surveillance of penicillin-binding protein 3 mutations in isolates from Japan. Antimicrob Agents Chemother. 2006 Jul;50(7):2487-92. [PubMed:16801430]
Kind
Protein
Organism
Human
Pharmacological action
No
Actions
Inhibitor
General Function
Peroxidase activity
Specific Function
Part of the host defense system of polymorphonuclear leukocytes. It is responsible for microbicidal activity against a wide range of organisms. In the stimulated PMN, MPO catalyzes the production o...
Gene Name
MPO
Uniprot ID
P05164
Uniprot Name
Myeloperoxidase
Molecular Weight
83867.71 Da
References
  1. Labro MT, el Benna J, Charlier N, Abdelghaffar H, Hakim J: Cefdinir (CI-983), a new oral amino-2-thiazolyl cephalosporin, inhibits human neutrophil myeloperoxidase in the extracellular medium but not the phagolysosome. J Immunol. 1994 Mar 1;152(5):2447-55. [PubMed:8133056]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Symporter activity
Specific Function
Sodium-ion dependent, high affinity carnitine transporter. Involved in the active cellular uptake of carnitine. Transports one sodium ion with one molecule of carnitine. Also transports organic cat...
Gene Name
SLC22A5
Uniprot ID
O76082
Uniprot Name
Solute carrier family 22 member 5
Molecular Weight
62751.08 Da
References
  1. Ganapathy ME, Huang W, Rajan DP, Carter AL, Sugawara M, Iseki K, Leibach FH, Ganapathy V: beta-lactam antibiotics as substrates for OCTN2, an organic cation/carnitine transporter. J Biol Chem. 2000 Jan 21;275(3):1699-707. [PubMed:10636865]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name
SLC15A1
Uniprot ID
P46059
Uniprot Name
Solute carrier family 15 member 1
Molecular Weight
78805.265 Da
References
  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716]
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]
  3. Tsuji A: Transporter-mediated Drug Interactions. Drug Metab Pharmacokinet. 2002;17(4):253-74. [PubMed:15618677]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Peptide:proton symporter activity
Specific Function
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name
SLC15A2
Uniprot ID
Q16348
Uniprot Name
Solute carrier family 15 member 2
Molecular Weight
81782.77 Da
References
  1. Ganapathy ME, Prasad PD, Mackenzie B, Ganapathy V, Leibach FH: Interaction of anionic cephalosporins with the intestinal and renal peptide transporters PEPT 1 and PEPT 2. Biochim Biophys Acta. 1997 Mar 13;1324(2):296-308. [PubMed:9092716]
  2. Terada T, Saito H, Mukai M, Inui K: Recognition of beta-lactam antibiotics by rat peptide transporters, PEPT1 and PEPT2, in LLC-PK1 cells. Am J Physiol. 1997 Nov;273(5 Pt 2):F706-11. [PubMed:9374833]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:39